#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/27/1502782.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502782
loop_
_publ_author_name
'Nagai, Atsushi'
'Chujo, Yoshiki'
_publ_section_title
;
 Aromatic Ring-Fused BODIPY-Based Conjugated Polymers Exhibiting Narrow
 Near-Infrared Emission Bands
;
_journal_issue                   1
_journal_name_full               Macromolecules
_journal_page_first              193
_journal_paper_doi               10.1021/ma901449c
_journal_volume                  43
_journal_year                    2010
_chemical_formula_sum            'C29 H17 B F2 I2 N2'
_chemical_formula_weight         696.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.611(3)
_cell_angle_beta                 93.971(3)
_cell_angle_gamma                92.562(4)
_cell_formula_units_Z            2
_cell_length_a                   7.4515(7)
_cell_length_b                   11.6557(14)
_cell_length_c                   15.1935(15)
_cell_measurement_temperature    93(2)
_cell_volume                     1228.8(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11582
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  0.7813
_exptl_absorpt_correction_T_min  0.3568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.140
_refine_diff_density_min         -1.856
_refine_diff_density_rms         0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0112P)²+31.5191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                4009
_reflns_number_total             5402
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ma901449c_si_001.cif
_cod_data_source_block           indo
_cod_original_sg_symbol_Hall     -p_1
_cod_original_sg_symbol_H-M      p_-1
_cod_database_code               1502782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.78404(9) -0.38500(6) 0.02051(5) 0.02850(19) Uani 1 1 d .
I2 I 0.32846(10) -0.17556(7) 0.01345(5) 0.0321(2) Uani 1 1 d .
F3 F 0.6236(8) -0.2217(5) 0.5675(4) 0.0291(13) Uani 1 1 d .
F4 F 0.8715(9) -0.2669(5) 0.4850(4) 0.0318(14) Uani 1 1 d .
C39 C 0.9211(13) -0.2790(9) 0.1530(6) 0.025(2) Uani 1 1 d .
C8 C 0.9108(13) -0.1131(9) 0.8153(7) 0.023(2) Uani 1 1 d .
H1 H 0.8623 -0.0376 0.8487 0.028 Uiso 1 1 calc R
C9 C 0.9431(13) 0.2775(9) 0.6974(7) 0.022(2) Uani 1 1 d .
H2 H 0.9086 0.3197 0.6563 0.027 Uiso 1 1 calc R
C10 C 1.0218(13) 0.3419(9) 0.7879(7) 0.024(2) Uani 1 1 d .
H3 H 1.0371 0.4291 0.8100 0.029 Uiso 1 1 calc R
C11 C 0.6746(12) -0.0365(8) 0.4269(7) 0.0192(18) Uani 1 1 d .
C12 C 0.9696(12) 0.0881(8) 0.7313(6) 0.0185(18) Uani 1 1 d .
N7 N 0.6550(10) -0.1512(7) 0.4343(5) 0.0183(16) Uani 1 1 d .
C14 C 0.9150(13) 0.1493(9) 0.6672(7) 0.0213(19) Uani 1 1 d .
C15 C 0.5730(13) -0.2324(9) 0.3532(7) 0.0217(19) Uani 1 1 d .
N8 N 0.8447(10) -0.0572(7) 0.5934(5) 0.0181(15) Uani 1 1 d .
C17 C 0.8388(13) 0.0565(8) 0.5830(6) 0.0196(18) Uani 1 1 d .
C18 C 0.5473(13) -0.4508(9) 0.2472(7) 0.027(2) Uani 1 1 d .
H4 H 0.5985 -0.4246 0.2013 0.032 Uiso 1 1 calc R
C19 C 0.9394(15) -0.1973(10) 0.8589(8) 0.032(2) Uani 1 1 d .
H5 H 0.9041 -0.1816 0.9207 0.038 Uiso 1 1 calc R
C20 C 0.5378(13) -0.1693(9) 0.2888(6) 0.022(2) Uani 1 1 d .
C21 C 0.9523(12) -0.1376(9) 0.7228(7) 0.022(2) Uani 1 1 d .
C22 C 1.0600(15) -0.3322(9) 0.7193(8) 0.031(2) Uani 1 1 d .
H6 H 1.1096 -0.4075 0.6864 0.037 Uiso 1 1 calc R
C23 C 1.0562(13) 0.1541(9) 0.8219(7) 0.0219(19) Uani 1 1 d .
H7 H 1.0966 0.1139 0.8634 0.026 Uiso 1 1 calc R
C24 C 0.4510(14) -0.1234(10) 0.1530(7) 0.027(2) Uani 1 1 d .
C25 C 0.4415(13) -0.4045(9) 0.4003(7) 0.023(2) Uani 1 1 d .
H8 H 0.4186 -0.3466 0.4598 0.028 Uiso 1 1 calc R
B49 B 0.7476(15) -0.1816(10) 0.5207(7) 0.020(2) Uani 1 1 d .
C27 C 0.5186(14) -0.0003(10) 0.1981(7) 0.026(2) Uani 1 1 d .
H9 H 0.5120 0.0552 0.1650 0.031 Uiso 1 1 calc R
C28 C 0.5938(12) 0.0398(9) 0.2893(6) 0.0208(19) Uani 1 1 d .
H10 H 0.6387 0.1230 0.3208 0.025 Uiso 1 1 calc R
C29 C 0.4998(14) -0.5737(10) 0.2255(7) 0.029(2) Uani 1 1 d .
H11 H 0.5201 -0.6316 0.1656 0.035 Uiso 1 1 calc R
C30 C 1.0274(13) -0.2485(9) 0.6740(7) 0.025(2) Uani 1 1 d .
H12 H 1.0557 -0.2663 0.6107 0.030 Uiso 1 1 calc R
C31 C 0.4214(15) -0.6131(10) 0.2922(8) 0.032(2) Uani 1 1 d .
H13 H 0.3868 -0.6977 0.2777 0.039 Uiso 1 1 calc R
C32 C 0.5216(13) -0.3634(9) 0.3356(7) 0.023(2) Uani 1 1 d .
C33 C 0.4551(13) -0.2087(10) 0.1959(7) 0.026(2) Uani 1 1 d .
H14 H 0.4045 -0.2906 0.1646 0.032 Uiso 1 1 calc R
C34 C 0.9217(12) -0.0408(9) 0.6824(6) 0.0194(19) Uani 1 1 d .
C35 C 0.7610(13) 0.0658(9) 0.5006(7) 0.0205(19) Uani 1 1 d .
C37 C 1.0205(15) -0.3060(10) 0.8121(8) 0.034(3) Uani 1 1 d .
H15 H 1.0481 -0.3612 0.8436 0.041 Uiso 1 1 calc R
C36 C 0.6025(12) -0.0452(9) 0.3345(6) 0.0200(19) Uani 1 1 d .
C38 C 0.3949(15) -0.5273(10) 0.3796(8) 0.032(2) Uani 1 1 d .
H16 H 0.3441 -0.5536 0.4257 0.039 Uiso 1 1 calc R
H17 H 0.765(11) 0.141(8) 0.490(6) 0.001(19) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C23 C39 C10 123.5(9) 2_756 2_756
C23 C39 I1 119.3(7) 2_756 .
C10 C39 I1 117.1(7) 2_756 .
C19 C8 C21 120.7(10) . .
C10 C9 C14 119.2(9) . .
C9 C10 C39 120.3(9) . 2_756
N7 C11 C35 121.9(8) . .
N7 C11 C36 108.9(8) . .
C35 C11 C36 129.1(9) . .
C23 C12 C34 132.0(8) . .
C23 C12 C14 121.4(9) . .
C34 C12 C14 106.6(8) . .
C15 N7 C11 109.6(8) . .
C15 N7 B49 126.8(8) . .
C11 N7 B49 122.9(7) . .
C9 C14 C17 134.6(9) . .
C9 C14 C12 118.9(9) . .
C17 C14 C12 106.5(8) . .
N7 C15 C20 108.4(9) . .
N7 C15 C32 125.5(8) . .
C20 C15 C32 126.1(9) . .
C34 N8 C17 109.2(7) . .
C34 N8 B49 125.5(8) . .
C17 N8 B49 124.5(8) . .
C35 C17 N8 120.7(8) . .
C35 C17 C14 130.1(9) . .
N8 C17 C14 109.2(8) . .
C29 C18 C32 121.4(10) . .
C8 C19 C37 120.1(11) . .
C33 C20 C36 119.8(9) . .
C33 C20 C15 132.4(10) . .
C36 C20 C15 107.9(8) . .
C8 C21 C30 119.6(9) . .
C8 C21 C34 117.1(9) . .
C30 C21 C34 123.3(9) . .
C37 C22 C30 120.5(10) . .
C39 C23 C12 116.6(9) 2_756 .
C33 C24 C27 123.4(10) . .
C33 C24 I2 119.0(8) . .
C27 C24 I2 117.6(7) . .
C38 C25 C32 121.1(10) . .
F3 B49 F4 112.3(8) . .
F3 B49 N8 106.9(7) . .
F4 B49 N8 110.9(8) . .
F3 B49 N7 112.0(8) . .
F4 B49 N7 107.3(7) . .
N8 B49 N7 107.3(7) . .
C28 C27 C24 120.3(9) . .
C27 C28 C36 117.8(9) . .
C18 C29 C31 119.7(10) . .
C22 C30 C21 119.4(10) . .
C38 C31 C29 119.2(10) . .
C25 C32 C18 117.8(9) . .
C25 C32 C15 123.7(9) . .
C18 C32 C15 118.4(9) . .
C24 C33 C20 116.8(10) . .
N8 C34 C12 108.4(8) . .
N8 C34 C21 126.8(8) . .
C12 C34 C21 124.7(8) . .
C17 C35 C11 122.1(9) . .
C22 C37 C19 119.5(10) . .
C28 C36 C20 122.0(8) . .
C28 C36 C11 132.7(9) . .
C20 C36 C11 105.3(8) . .
C25 C38 C31 120.6(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C39 2.115(9) .
I2 C24 2.115(10) .
F3 B49 1.365(12) .
F4 B49 1.382(12) .
C39 C23 1.367(14) 2_756
C39 C10 1.402(14) 2_756
C8 C19 1.380(14) .
C8 C21 1.391(14) .
C9 C10 1.386(14) .
C9 C14 1.401(13) .
C10 C39 1.402(14) 2_756
C11 N7 1.383(12) .
C11 C35 1.408(13) .
C11 C36 1.434(13) .
C12 C23 1.411(13) .
C12 C34 1.437(13) .
C12 C14 1.443(13) .
N7 C15 1.345(12) .
N7 B49 1.596(13) .
C14 C17 1.414(13) .
C15 C20 1.435(13) .
C15 C32 1.481(14) .
N8 C34 1.377(11) .
N8 C17 1.392(12) .
N8 B49 1.586(13) .
C17 C35 1.384(13) .
C18 C29 1.376(15) .
C18 C32 1.403(14) .
C19 C37 1.404(16) .
C20 C33 1.407(14) .
C20 C36 1.411(13) .
C21 C30 1.407(13) .
C21 C34 1.481(13) .
C22 C37 1.389(16) .
C22 C30 1.399(14) .
C23 C39 1.367(14) 2_756
C24 C33 1.368(14) .
C24 C27 1.407(15) .
C25 C38 1.376(14) .
C25 C32 1.394(14) .
C27 C28 1.365(13) .
C28 C36 1.393(13) .
C29 C31 1.402(16) .
C31 C38 1.386(16) .
